The last few years, I haven’t been travelling much (for… obvious reasons). Now that travel is feeling like a reality again, I realise my perception of it has changed. The idea of spending thousands of dollars to stick myself in a metal tube with hundreds of strangers for 10+ hours seems unappealing, especially when I’d have to leave Fyodor Dogstoyevsky at home. I’d much rather jump in a car, with my canine sidekick, and start our adventure straight away – plus, spend our precious tourist dollars closer to home, in communities that have been ravaged by climate emergencies. I went looking for literary inspiration, and turned up these ten books about road trips.

10 Books About Road Trips - Book List - Keeping Up With The Penguins
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On The Road by Jack Kerouac

On The Road - Jack Kerouac - book laid on wooden table - Keeping Up With The Penguins

Every list of books about road trips begins with On The Road – it’s truly iconic. This classic of the Beat generation is based on 20-something Kerouac’s travels across the United States in the years following WWII. In fact, it’s more than “based on”: it’s basically a true story with a bunch of fake names to protect the guilty. From New York to San Francisco and back again, Virginia to New Orleans, Denver to Chicago and Detroit, across Texas and down into Mexico, Kerouac (ahem, I mean “Sal”) and his friends criss-cross the country in a hodge-podge fashion, always seeking adventure and finding trouble. I’m not sure it’s one I’d like to emulate exactly, but it’s certainly romantic in theory. Read my full review of On The Road here.

Zen and The Art of Motorcycle Maintenance by Robert Pirsig

Zen and the Art of Motorcycle Maintenance - Robert M Pirsig - Book Laid on Wooden Table - Keeping Up With The Penguins

Zen and The Art of Motorcycle Maintenance is a pop psychology/philosophy book, masquerading as one of the classic books about road trips. A father and son undertake a summer trip on motorcycles, forcing them to confront the ‘confusion of existence’. They discover how to reconcile the silences between them and between their spiritual lives through (you guessed it) motorcycle maintenance, an unfortunate reality of motorcycle journeys turned beautiful metaphor. This book also holds the dubious honour of being (officially!) the most-often rejected best-seller, having been turned down an astonishing 121 times before it found a publisher and went on to sell over five million copies.

Into The Wild by Jon Krakauer

Into The Wild - Jon Krakauer - Keeping Up With The Penguins

Of all the books about road trips, this is my favourite example of one gone wrong. I first became familiar with the story of Christopher McCandless when my husband encouraged (read: forced) me to sit and watch the film adaptation of Jon Krakauer’s book Into The Wild. Whichever medium you choose to learn the story, it’s the same. A privileged white boy takes it into his head that he needs to escape his suffocating life of comfort, and takes off across the country completely unprepared. In a display of hubris the likes of which we haven’t seen since the Greek tragedies, McCandless takes a break from hitchhiking and civilisation to hike off into the wildnerness, never to be seen alive again. This is a frustrating read about a feckless young man, and an excellent example of what not to do.

Station Eleven by Emily St John Mandel

Station Eleven - Emily St John Mandel - Keeping Up With The Penguins

One of the more bizarre books about road trips is Station Eleven, Emily St John Mandel’s vision of a post-pandemic world with a travelling troupe performing Shakespeare for the remainders of humanity. This one kind of picks up where Fahrenheit 451 leaves off, a small band of true believers dedicating what’s left of their lives to keeping the arts alive in the wake of disaster. The story jumps back and forth, between the pre- and post-pandemic years, so it can be a little confusing – not to mention triggering for those of us still living it. But it’s a rich and fascinating book, one that shows the desire to hit the road never really dies.

The Road by Cormac McCarthy

The Road - Cormac McCarthy - Keeping Up With The Penguins

Speaking of post-apocalyptic dystopian books about road trips, you can’t go past The Road, Cormac McCarthy’s most widely-read novel. The father-son motif features in this one, as well. A father and son (maybe? kind of? it’s never really clear) follow the road through the landscape of a ravaged America, hoping to reach the coast (again, for reasons not really known). They face danger at every turn, as if the perilous climate weren’t risk enough, and all they have to sustain them is each other. This isn’t exactly an uplifting read, but it does interrogate the depths of our connections with one another. It was enough for Oprah to select it as an unlikely Book Club pick, anyhow!

As I Lay Dying by William Faulkner

As I Lay Dying - William Faulkner - Keeping Up With The Penguins

As I Lay Dying is one of the books about road trips for bummer reasons (as opposed to the devil-may-care let’s-adventure have-fun variety). Addie, the matriarch of a disadvantaged Southern family, ails and dies in the opening chapter, laying on her bed and listening to her family chop wood for her coffin outside her bedroom window. Her final wish is to be laid to rest in her hometown of Jefferson, Mississippi. So, her family gathers their meager resources and hoist the coffin onto their shoulders, and make their way across the American South. It’s a fraught journey, with family drama playing out at every turn, and the hardships of the journey intensifying it all. Read my full review of As I Lay Dying here.

Wild by Cheryl Strayed

Wild - Cheryl Strayed - book laid on wooden table - Keeping Up With The Penguins

Alright, strictly speaking, Wild isn’t so much one of the books about road trips as it is one of the books about hiking trails – but Strayed spends considerable time in cars, and a road’s a road’s a road, isn’t it? She set out on a grueling trek (1,100 miles!) along the Pacific Crest Trail almost entirely unprepared, with an overstuffed backpack and zero training. Along the way, she loses a shoe, grieves her mother, runs out of money, reads poetry, and learns a whole heck of a lot real fast. It’s basically Eat, Pray, Love meets Survivor, one that will make you think about what you’re really looking for next time the road calls to you. Read my full review of Wild here.

Paper Towns by John Green

Paper Towns - John Green - book laid on a wooden table - Keeping Up With The Penguins

Paper Towns requires you to suspend your disbelief a bit. The nerdy, underappreciated boy-next-door (Quentin “Q” Jacobsen) “loves” Margo Roth Spiegelman from afar for years. She is (surprise, surprise) beautiful, mysterious, and edgy. Margo goes missing, and Quentin goes looking for her, following her trail of clues. I mean, I’ve never met a teenager with enough foresight to leave complex metaphorical breadcrumbs when they run away, and, indeed, why would they? The whole point of running away is, y’know, to not get caught. Still, it’s what John Green went with, and it’s one of the most popular young adult books about road trips, so I’m hardly in a position to turn my nose up. Read my full review of Paper Towns here.

(John Green wrote another popular young adult book about a road trip, too: An Abundance Of Katherines.)

The Other Side Of Beautiful by Kim Lock

The Other Side Of Beautiful - Kim Lock - Keeping Up With The Penguins

Sometimes, you pick up a book and its premise resonates in a way neither you nor the author anticipated. That’s what happened for me with The Other Side Of Beautiful. It opens with a really tight first chapter, one that will grab you and not let go: Mercy watches her house burn down, forcing her out into the world that her agoraphobia has kept her from for years. She finds herself in a camper van, with her ever-faithful sausage dog Wasabi (my absolute hands-down favourite character) by her side, driving the length of Australia, from Adelaide to Darwin. I feel so lucky to have found a book about my dream road trip – canine companion included! Read my full review of The Other Side Of Beautiful here.

The Grapes Of Wrath by John Steinbeck

The Grapes Of Wrath - John Steinbeck - Book Laid on Wooden Table - Keeping Up With The Penguins

This story of a migrant family pulling themselves up out of the Dust Bowl during the Great Depression seems eerily relevant and poignant in a post-Trump and post-Brexit world. The Grapes Of Wrath is another one of the iconic American books about road trips, this time featuring the impoverished Joad family and their pursuit of the American dream (you know, having enough money to feed themselves). They pile into a truck and drive from Oklahoma to California, where they’ve heard there’s jobs aplenty, only to discover that they aren’t the only family who had the idea to look for work in the Golden State. Read my full review of The Grapes Of Wrath here.